


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810010718/ds2025sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810010718/ds2025Isup2.hkl |
CCDC reference: 774375
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.028
- wR factor = 0.070
- Data-to-parameter ratio = 34.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 67
Alert level G PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety C17
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was obtained according to the procedure: A mixture of the para-cresol 1,08 g (10,0 mmol) and 3,4'-dibromopropiophenone 0,59 g (2,0 mmol) in BF3.OEt2 (20 ml) was heated at 60 °C and stirred for 8 h. The products of reaction were extracted from the mixtures with chloroform. Titled product was separated by column chromatography on silica gel with hexane/methyl chloride/acetone (10:1:1 v/v/v) as eluent (Scheme). Crystals suitable for X-ray structure analysis were obtained by slow evaporation from the eluent at room temperature. Structure of the titled product was confirmed by means of the 1H NMR and 13 C NMR spectra. 1H NMR (600 MHz, CDCl3 δ, p.p.m.): 6.81 (s, 1H, H3), 7.48 (d, 1H, J=8.56 Hz, H8), 7.54 (dd, 1H, J=8.56, 2.12 Hz, H7), 7.68 (m, 2H Wh=8.60 Hz, H5' and H7'), 7.80 (m, 2H, Wh=8.60 Hz, H2' and H6'), 8.04 (d, 1H, J=2.12 Hz, H-5). 13 C NMR (150 MHz, CDCl3 δ, p.p.m.): 20.98 (-CH3); 107.55 (C3); 117.83 (C8); 123.56 (C10); 125.13 (C5); 126.25 (C6); 127.71 (C3' i C5'); 130.84 (C1'); 132.35 (C2' i C6'); 135.21 (C7); 135.47 (C4'); 154.48 (C9) 162.23 (C2); 178.48 (C4).
Non-hydrogen atoms were refined with anisotropic displacement parameters. All H atoms were placed at calculated positions and were treated as riding atoms, with C—H distances of 0.95 - 1.00 Å.
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![]() | Fig. 1. Selected view of 4'-bromo-6-methyloflavone with the numbering scheme employed. |
![]() | Fig. 2. Molecular packing of 4'-bromo-6-methyloflavone. |
C16H11BrO2 | F(000) = 632 |
Mr = 315.16 | Dx = 1.645 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11464 reflections |
a = 13.759 (3) Å | θ = 3.0–36.9° |
b = 6.873 (2) Å | µ = 3.22 mm−1 |
c = 13.460 (2) Å | T = 100 K |
β = 90.25 (3)° | Plate, colorless |
V = 1272.8 (5) Å3 | 0.31 × 0.29 × 0.04 mm |
Z = 4 |
Kuma KM-4-CCD diffractometer | 5962 independent reflections |
Radiation source: fine-focus sealed tube | 3659 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ω scan | θmax = 36.0°, θmin = 3.0° |
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)] | h = −22→22 |
Tmin = 0.474, Tmax = 0.893 | k = −11→10 |
25822 measured reflections | l = −21→22 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.070 | H-atom parameters constrained |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0385P)2] where P = (Fo2 + 2Fc2)/3 |
5962 reflections | (Δ/σ)max < 0.001 |
172 parameters | Δρmax = 0.69 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
C16H11BrO2 | V = 1272.8 (5) Å3 |
Mr = 315.16 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.759 (3) Å | µ = 3.22 mm−1 |
b = 6.873 (2) Å | T = 100 K |
c = 13.460 (2) Å | 0.31 × 0.29 × 0.04 mm |
β = 90.25 (3)° |
Kuma KM-4-CCD diffractometer | 5962 independent reflections |
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)] | 3659 reflections with I > 2σ(I) |
Tmin = 0.474, Tmax = 0.893 | Rint = 0.047 |
25822 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.070 | H-atom parameters constrained |
S = 0.88 | Δρmax = 0.69 e Å−3 |
5962 reflections | Δρmin = −0.37 e Å−3 |
172 parameters |
Experimental. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Br | 0.122301 (8) | 0.12666 (2) | 0.048602 (10) | 0.02299 (4) | |
O1 | 0.59232 (6) | 0.12638 (15) | 0.20324 (6) | 0.01526 (15) | |
C2 | 0.51619 (8) | 0.12091 (19) | 0.26748 (8) | 0.01346 (19) | |
C3 | 0.52887 (8) | 0.1170 (2) | 0.36736 (8) | 0.0158 (2) | |
H3A | 0.4733 | 0.1138 | 0.4089 | 0.019* | |
O4 | 0.63780 (7) | 0.11445 (16) | 0.50391 (6) | 0.02132 (18) | |
C4 | 0.62442 (8) | 0.1176 (2) | 0.41278 (9) | 0.0152 (2) | |
C5 | 0.80289 (8) | 0.1197 (2) | 0.37337 (9) | 0.0158 (2) | |
H5A | 0.8173 | 0.1160 | 0.4424 | 0.019* | |
C6 | 0.87838 (8) | 0.1235 (2) | 0.30587 (9) | 0.0173 (2) | |
C7 | 0.85504 (9) | 0.1311 (2) | 0.20364 (9) | 0.0188 (2) | |
H7A | 0.9062 | 0.1348 | 0.1565 | 0.023* | |
C8 | 0.76018 (9) | 0.1335 (2) | 0.17014 (9) | 0.0179 (2) | |
H8A | 0.7459 | 0.1396 | 0.1011 | 0.021* | |
C9 | 0.70523 (8) | 0.1212 (2) | 0.34182 (8) | 0.01366 (19) | |
C10 | 0.68548 (8) | 0.1267 (2) | 0.24016 (9) | 0.01469 (19) | |
C11 | 0.42181 (8) | 0.12034 (19) | 0.21497 (8) | 0.01378 (19) | |
C12 | 0.41819 (9) | 0.1370 (2) | 0.11092 (9) | 0.0170 (2) | |
H12A | 0.4768 | 0.1477 | 0.0743 | 0.020* | |
C13 | 0.32929 (9) | 0.1380 (2) | 0.06124 (9) | 0.0181 (2) | |
H13A | 0.3269 | 0.1486 | −0.0091 | 0.022* | |
C14 | 0.24418 (8) | 0.1234 (2) | 0.11563 (9) | 0.0169 (2) | |
C15 | 0.24576 (9) | 0.1070 (2) | 0.21903 (10) | 0.0184 (2) | |
H15A | 0.1869 | 0.0980 | 0.2553 | 0.022* | |
C16 | 0.33448 (9) | 0.1041 (2) | 0.26785 (9) | 0.0166 (2) | |
H16A | 0.3363 | 0.0910 | 0.3381 | 0.020* | |
C17 | 0.98418 (9) | 0.1213 (2) | 0.33957 (10) | 0.0217 (2) | |
H17A | 0.9871 | 0.1160 | 0.4123 | 0.033* | |
H17B | 1.0167 | 0.2396 | 0.3163 | 0.033* | |
H17C | 1.0168 | 0.0069 | 0.3118 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.01513 (6) | 0.02745 (7) | 0.02633 (7) | 0.00270 (6) | −0.00771 (4) | −0.00266 (6) |
O1 | 0.0108 (3) | 0.0227 (4) | 0.0123 (3) | −0.0008 (4) | −0.0008 (3) | 0.0003 (4) |
C2 | 0.0130 (4) | 0.0128 (5) | 0.0145 (5) | −0.0002 (5) | 0.0009 (4) | 0.0007 (5) |
C3 | 0.0135 (4) | 0.0200 (5) | 0.0139 (5) | −0.0007 (5) | 0.0013 (4) | 0.0001 (5) |
O4 | 0.0200 (4) | 0.0308 (5) | 0.0132 (4) | −0.0045 (4) | −0.0010 (3) | 0.0008 (4) |
C4 | 0.0155 (5) | 0.0155 (5) | 0.0145 (5) | −0.0015 (5) | −0.0006 (4) | 0.0003 (5) |
C5 | 0.0146 (5) | 0.0159 (5) | 0.0169 (5) | −0.0008 (5) | −0.0031 (4) | −0.0006 (5) |
C6 | 0.0128 (4) | 0.0177 (5) | 0.0215 (5) | −0.0009 (5) | −0.0020 (4) | −0.0009 (5) |
C7 | 0.0137 (5) | 0.0232 (6) | 0.0195 (5) | −0.0004 (5) | 0.0019 (4) | −0.0014 (6) |
C8 | 0.0147 (5) | 0.0239 (6) | 0.0150 (5) | −0.0004 (5) | 0.0004 (4) | −0.0012 (5) |
C9 | 0.0124 (4) | 0.0143 (5) | 0.0144 (5) | −0.0010 (5) | −0.0005 (4) | 0.0002 (5) |
C10 | 0.0115 (4) | 0.0157 (5) | 0.0168 (5) | −0.0008 (5) | −0.0012 (4) | −0.0007 (5) |
C11 | 0.0122 (4) | 0.0138 (5) | 0.0154 (5) | −0.0001 (5) | −0.0015 (4) | −0.0002 (5) |
C12 | 0.0149 (5) | 0.0191 (6) | 0.0171 (5) | −0.0007 (5) | −0.0005 (4) | 0.0017 (5) |
C13 | 0.0178 (5) | 0.0195 (6) | 0.0170 (5) | −0.0008 (5) | −0.0031 (4) | 0.0008 (5) |
C14 | 0.0144 (5) | 0.0160 (5) | 0.0203 (5) | 0.0017 (5) | −0.0046 (4) | −0.0008 (5) |
C15 | 0.0139 (5) | 0.0196 (6) | 0.0216 (6) | 0.0003 (5) | −0.0001 (4) | −0.0012 (5) |
C16 | 0.0138 (5) | 0.0198 (6) | 0.0163 (5) | −0.0001 (5) | 0.0000 (4) | −0.0002 (5) |
C17 | 0.0140 (5) | 0.0270 (6) | 0.0240 (6) | 0.0002 (6) | −0.0036 (4) | −0.0022 (6) |
Br—C14 | 1.9008 (13) | C8—C10 | 1.3983 (16) |
O1—C2 | 1.3617 (14) | C8—H8A | 0.9500 |
O1—C10 | 1.3727 (14) | C9—C10 | 1.3944 (16) |
C2—C3 | 1.3551 (16) | C11—C16 | 1.4036 (17) |
C2—C11 | 1.4757 (16) | C11—C12 | 1.4059 (16) |
C3—C4 | 1.4475 (17) | C12—C13 | 1.3914 (17) |
C3—H3A | 0.9500 | C12—H12A | 0.9500 |
O4—C4 | 1.2397 (15) | C13—C14 | 1.3875 (17) |
C4—C9 | 1.4692 (16) | C13—H13A | 0.9500 |
C5—C6 | 1.3832 (17) | C14—C15 | 1.3964 (18) |
C5—C9 | 1.4075 (16) | C15—C16 | 1.3839 (17) |
C5—H5A | 0.9500 | C15—H15A | 0.9500 |
C6—C7 | 1.4126 (18) | C16—H16A | 0.9500 |
C6—C17 | 1.5228 (17) | C17—H17A | 0.9800 |
C7—C8 | 1.3792 (17) | C17—H17B | 0.9800 |
C7—H7A | 0.9500 | C17—H17C | 0.9800 |
C2—O1—C10 | 119.33 (9) | O1—C10—C8 | 116.36 (10) |
C3—C2—O1 | 122.30 (10) | C9—C10—C8 | 121.44 (10) |
C3—C2—C11 | 125.75 (11) | C16—C11—C12 | 119.01 (11) |
O1—C2—C11 | 111.95 (9) | C16—C11—C2 | 120.72 (10) |
C2—C3—C4 | 122.12 (11) | C12—C11—C2 | 120.27 (10) |
C2—C3—H3A | 118.9 | C13—C12—C11 | 120.42 (11) |
C4—C3—H3A | 118.9 | C13—C12—H12A | 119.8 |
O4—C4—C3 | 123.27 (11) | C11—C12—H12A | 119.8 |
O4—C4—C9 | 122.28 (11) | C14—C13—C12 | 119.23 (11) |
C3—C4—C9 | 114.45 (10) | C14—C13—H13A | 120.4 |
C6—C5—C9 | 121.35 (11) | C12—C13—H13A | 120.4 |
C6—C5—H5A | 119.3 | C13—C14—C15 | 121.48 (11) |
C9—C5—H5A | 119.3 | C13—C14—Br | 119.58 (9) |
C5—C6—C7 | 118.19 (11) | C15—C14—Br | 118.94 (9) |
C5—C6—C17 | 121.59 (11) | C16—C15—C14 | 118.97 (12) |
C7—C6—C17 | 120.23 (11) | C16—C15—H15A | 120.5 |
C8—C7—C6 | 121.99 (11) | C14—C15—H15A | 120.5 |
C8—C7—H7A | 119.0 | C15—C16—C11 | 120.88 (12) |
C6—C7—H7A | 119.0 | C15—C16—H16A | 119.6 |
C7—C8—C10 | 118.46 (11) | C11—C16—H16A | 119.6 |
C7—C8—H8A | 120.8 | C6—C17—H17A | 109.5 |
C10—C8—H8A | 120.8 | C6—C17—H17B | 109.5 |
C10—C9—C5 | 118.56 (10) | H17A—C17—H17B | 109.5 |
C10—C9—C4 | 119.58 (10) | C6—C17—H17C | 109.5 |
C5—C9—C4 | 121.87 (10) | H17A—C17—H17C | 109.5 |
O1—C10—C9 | 122.20 (10) | H17B—C17—H17C | 109.5 |
C10—O1—C2—C3 | 0.45 (19) | C4—C9—C10—O1 | −0.9 (2) |
C10—O1—C2—C11 | −179.69 (13) | C5—C9—C10—C8 | −0.9 (2) |
O1—C2—C3—C4 | −0.3 (2) | C4—C9—C10—C8 | 178.91 (13) |
C11—C2—C3—C4 | 179.90 (13) | C7—C8—C10—O1 | −179.04 (14) |
C2—C3—C4—O4 | 179.89 (13) | C7—C8—C10—C9 | 1.2 (2) |
C2—C3—C4—C9 | −0.5 (2) | C3—C2—C11—C16 | −3.7 (2) |
C9—C5—C6—C7 | 0.7 (2) | O1—C2—C11—C16 | 176.44 (12) |
C9—C5—C6—C17 | −179.82 (14) | C3—C2—C11—C12 | 175.99 (13) |
C5—C6—C7—C8 | −0.4 (2) | O1—C2—C11—C12 | −3.86 (18) |
C17—C6—C7—C8 | −179.95 (14) | C16—C11—C12—C13 | 0.2 (2) |
C6—C7—C8—C10 | −0.5 (2) | C2—C11—C12—C13 | −179.51 (13) |
C6—C5—C9—C10 | 0.0 (2) | C11—C12—C13—C14 | 0.3 (2) |
C6—C5—C9—C4 | −179.84 (13) | C12—C13—C14—C15 | −0.2 (2) |
O4—C4—C9—C10 | −179.34 (13) | C12—C13—C14—Br | 179.51 (11) |
C3—C4—C9—C10 | 1.0 (2) | C13—C14—C15—C16 | −0.4 (2) |
O4—C4—C9—C5 | 0.5 (2) | Br—C14—C15—C16 | 179.84 (11) |
C3—C4—C9—C5 | −179.17 (13) | C14—C15—C16—C11 | 1.0 (2) |
C2—O1—C10—C9 | 0.1 (2) | C12—C11—C16—C15 | −0.8 (2) |
C2—O1—C10—C8 | −179.67 (12) | C2—C11—C16—C15 | 178.85 (14) |
C5—C9—C10—O1 | 179.28 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O4i | 0.95 | 2.49 | 3.2904 (17) | 142 |
C16—H16A···O4i | 0.95 | 2.58 | 3.4394 (16) | 151 |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H11BrO2 |
Mr | 315.16 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 13.759 (3), 6.873 (2), 13.460 (2) |
β (°) | 90.25 (3) |
V (Å3) | 1272.8 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.22 |
Crystal size (mm) | 0.31 × 0.29 × 0.04 |
Data collection | |
Diffractometer | Kuma KM-4-CCD diffractometer |
Absorption correction | Analytical [CrysAlis RED (Oxford Diffraction, 2009); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)] |
Tmin, Tmax | 0.474, 0.893 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25822, 5962, 3659 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.827 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.070, 0.88 |
No. of reflections | 5962 |
No. of parameters | 172 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.69, −0.37 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Bruker, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O4i | 0.95 | 2.49 | 3.2904 (17) | 142.2 |
C16—H16A···O4i | 0.95 | 2.58 | 3.4394 (16) | 151.2 |
Symmetry code: (i) −x+1, −y, −z+1. |
Cg(1) and Cg(2) are the centroids of the C5–C10 and C11–C16 rings, respectively. |
Cg(I) | Cg(J) | Cg–Cg | Alpha | CgI_perp | CgJ_Perp | Slippage |
Cg(1) | Cg(2)i | 3.895 | 7.13 (3) | 3.579 (2) | -3.430 (2) | 1.84 |
Cg(1) | Cg(2)ii | 3.843 | 7.13 (3) | -3.266 (2) | 3.438 (2) | 1.72 |
Notes: Cg–Cg = distance between ring centroids; Alpha = dihedral angle between planes I and J; CgI_Perp = perpendicular distance of Cg(I) on ring J; CgJ_Perp = perpendicular distance of Cg(J) on ring I; Slippage = distance between Cg(I) and perpendicular projection of Cg(J) on Ring I. Symmetry codes: (i) 1-x, -0.5+y, 0.5-z, (ii) 1-x, 0.5+y, 0.5-z. |
Seeds, fruit skin, bark and flowers of most plants contain significant amount of flavonoids. They have been classified to one subclass of flavonoids according to their chemical structures (Hsiao et al., 2007). Several naturally occurring and synthetic flavones are well know in respect to their anti-oxidant, anti-neoplastic, anti-malarial, anti-inflammatory and insecticidal activity (Manthey et al., 2001; Millot et al., 2009; Moulari et al., 2006). Halogenoflavones have been used as precursors for the synthesis of a variety of bioactive organic compounds including biflavodoids (Ren et al., 2003; Moon et al., 2007). The title compound is a flavone derivative with 4'-bromo and 6-methyl substituents in the biologically active region (Scheme) (Middleton et al., 2000).
Crystal structures of the following related flavones were reported: 7-hydroxyflavone monohydrate (Kumar et al., 1998), 6-(3-hydroxy-3-methylbut-1-ynyl)-flavone and 6-(3-methylbut-3-en-1-ynyl)-flavone (Artali et al., 2003), 2-phenyl-6-hydroxy-4H-1-benzopyran-4-one (6-hydroxyflavone) (Białońska et al., 2007), 3,5,4'-trihydroxy-6,7-dimethoxy-flavone (Eupalitin) (Ghalib et al., 2010).
Structure of 2-(4-bromophenyl)-6-methyl-4H-1-benzopyran-4-one with the numbering scheme employed is presented in Fig. 1 Molecules of the titled compound form ribbons stabilized by π–π stacking interactions exteded along the [010] direction (Table 2). The neighboring ribbons are linked by C—H···O hydrogen bonds, in which the carbonyl O4 atom is their acceptor (Table 1). The resulting layers perpendicular to the [100] direction (Fig. 2).